Best Cruises & Sailing Tours in Chicago

A truly special event sail! ⛵✨ During the summer, every Wednesday and Saturday night, the Tall Ship Windy sails from Navy Pier for our guests to enjoy the spectacular night fireworks from the best seat in town. 🎆 Enjoy the amenities of the 148-foot, four-masted Schooner that is the official ship of the City of Chicago. 🚢 Sail from Navy Pier and take in the picturesque Chicago skyline. 🏙️ Experience one of the best summer fireworks displays in the nation aboard a world-class tall ship! 🎇 Then, get your history fix with a rousing rendition of traditional shipboard working songs against the backdrop of the brilliantly lit Chicago skyline. 🎶 This is a one-of-a-kind, uniquely Chicago experience! 🏴‍☠️ The Wednesday Fireworks Boat Tour departs promptly at 8:45 PM, and the Saturday tour departs at 9:15 PM. ⏰

Our popular 90-minute daytime river and lake tour, the Urban Adventure Cruise, delights family members of all ages with incredible views of Chicago's world-renowned architecture and stunning skyline. Lively, knowledgeable tour guides bring Chicago’s rich history to life with fun stories and interesting facts. Relax and unwind on a scenic tour of the city from the unique perspective of the Chicago River and Lake Michigan. Welcome aboard!

The Chicago Architecture Center River Cruise aboard Chicago's First Lady has long been the gold standard among all Chicago tour experiences, and is the only Chicago architecture boat tour led by highly trained expert docents. On this 90-minute cruise, you will enjoy an overview of historic and modern architectural styles including stories about the people who designed and built Chicago. As a certified nonprofit, all ticket purchases directly support education efforts and community engagement projects. No visit to Chicago is complete without experiencing this award winning tour, so accept no substitutes.

Experience the stunning beauty of Chicago on a captivating cruise along the historic Chicago River. This architectural tour takes you down the main branch of the river, up the north branch to the East Bank Club, and then south past the iconic Willis Tower (Sears Tower) to the historic Old Post Office Building. Marvel at the magnificent city skyline as you pass by over 40 notable buildings, including: John Hancock Center: An iconic skyscraper that defines the Chicago skyline. Wrigley Building: Known for its distinctive white facade and clock tower. As you sail, an expert architecture guide will provide fascinating insights into the distinctive designs and history of these architectural marvels. Whether you're a local or visiting for the first time, this tour offers a unique perspective on one of the world's most beautiful cities. Sit back, relax, and let the architectural wonders of Chicago unfold before your eyes.

All Day! Sundays are Fun-Days aboard the floating tiki bar! 🍹 Experience the Chicago River in a unique Island Party style. 🌴 Our floating tiki bar lets you soak in all the sights and sounds while relaxing with a refreshing beverage. 🌊 Have questions about the buildings and landmarks? 🏙️ Our friendly staff is here to provide helpful answers and enhance your experience. 🌞 Don’t miss out on this unforgettable Sunday adventure! 🎉

Glide along the Chicago River and Lakefront while being dazzled by the sparkle of the city at night! 🌆 Enjoy breathtaking views of dramatic skyscrapers and Buckingham Fountain's spectacular light display. 💦 Hear lively commentary as you feel the night breeze and witness Chicago’s skyline transformed into a glittering jewel. ✨ This is a one-of-a-kind experience that belongs on your Chicago bucket list! ✅ Family-friendly cruises are our specialty, making it perfect for all ages. 👨‍👩‍👧‍👦 Don’t miss out on this unforgettable adventure at Chicago by Night: 90 Minute River and Lakefront Cruise! 🌟

Set sail on the Chicago River with an exclusive vibe on a vintage yacht!🛥️ It's the Chicago essential with a twist – glide past the river's stunning skyline and dive into the tales of over 50 iconic buildings.🏙️ We dish out all the deets on their architecture and history, making sure you finish your cruise feeling like a Chi-Town pro. Get your tickets for the Chicago River Architecture Tour Aboard a Historic Yacht!

Celebrate Independence Day with our Premier Dinner Cruise on Lake Michigan! 🎆 Enjoy a delicious plated dinner featuring freshly prepared entrees, salads, and desserts. 🍽️ Sip on creative cocktails, beer, and wine while taking in the spectacular views of the city skyline and local landmarks. 🌇 With a guaranteed table for your party size and live DJ entertainment, the atmosphere will be unforgettable! 🎶 After dinner, marvel at a fireworks display lighting up the night sky, honoring our nation's birthday. 🎇 Don’t forget, you must be 21 or older with valid ID to join this incredible 3-hour experience! 🌟

Be inspired by the captivating visual art that is Chicago’s legendary architecture, and the exceptional architects who created this ever-changing legacy! 🏙️ This comprehensive 90-minute tour navigates through the heart of the city on all three branches of the Chicago River. 🚤 Your professionally-trained architectural guide will share the story of more than 130 years of innovation in design, style, and technique. 🏛️ Discover why this architectural heritage is important today. 🌟 The Chicago River Architecture Tour is the most authentic and encompassing experience the city has to offer! 🎉

Set sail on the Lake Michigan Skyline Cruise and admire Chicago’s stunning lakefront sights! 🚢🌆 Enjoy incredible views of the city's famous skyscrapers from a unique perspective. 🏙️ This relaxing sightseeing tour allows you to soak in the beauty of the skyline while cruising along the lake. 🌊 Feel free to bring a lunch to savour as you enjoy the ride, and don’t forget to check out the drinks available at the onboard bar! 🍹 Perfect for a day of exploration and leisure on the water! 🎉